Sodium hydride → 3-(2-Methoxyethyl)thio-2-methyl-4-trifluoromethylbenzoic acid

HRID 548587

Reaktionsgleichung

Reaktionsgleichung von HRID 548587
F[C:2]1[C:3]([CH3:15])=[C:4]([CH:8]=[CH:9][C:10]=1[C:11]([F:14])([F:13])[F:12])[C:5]([OH:7])=[O:6].[H-].[Na+].[CH3:18][O:19][CH2:20][CH2:21][SH:22]>CN(C=O)C>[CH3:18][O:19][CH2:20][CH2:21][S:22][C:2]1[C:3]([CH3:15])=[C:4]([CH:8]=[CH:9][C:10]=1[C:11]([F:14])([F:13])[F:12])[C:5]([OH:7])=[O:6]

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 30146442-MethoxyethanethiolHCID 574577653-Fluoro-2-methyl-4-(trifluoromethyl)benzoic acid

Produkt 1

HCID 671584913-(2-Methoxyethyl)thio-2-methyl-4-trifluoromethylbenzoic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

1.45 g (6.53 mmol) of 3-fluoro-2-methyl-4-trifluoromethylbenzoic acid were initially charged in 40 ml of DMF. 809 mg (20.2 mmol) of NaH were added a little at a time. After the evolution of gas had ceased, 1.20 g (13.1 mmol) of 2-methoxyethanethiol were added a little at a time. The mixture was stirred at RT for 10 minutes and then heated at 80° C. for 15 h. The reaction mixture was cooled and concentrated under reduced pressure, and for work-up water was added and the mixture was acidified with 1M HCl. The product precipitated and was removed by filtration. The product was then washed with water and n-heptane. What was isolated were 1.7 g of the pure product.

Aufarbeitung

  1. temperatureheated at 80° C. for 15 h
  2. temperatureThe reaction mixture was cooled
  3. concentrationconcentrated under reduced pressure
  4. additionfor work-up water was added
  5. customThe product precipitated
  6. customwas removed by filtration
  7. washThe product was then washed with water and n-heptane
  8. customWhat was isolated

Quellen und Nachweise

ORD-Eintrag
ord-cd88a9c7f9b54c5abfbba09d68fbec05
Quelldatensatz
uspto-grants-2011_05
Patentnummer
US07943551B2

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